A busy street with a large clock, brick buildings, and cars.

Chelsea Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Chelsea holiday rentals

A modern living room with a sofa, coffee table, and a small table with books and a lamp. There is a kitchen area with cabinets, a refrigerator, and a microwave. A welcome sign is on the wall, and a basketball arcade game is visible.

1. Charming 2-bedroom condo in delightful Chelsea with WiFi, AC

Charming 2-bedroom condo in delightful Chelsea with WiFi, AC
Chelsea
8.6 out of 10, Excellent, (10 reviews)
"It was close to Boston and the airport"
United States
Lewis
The price is HK$1,192
HK$2,829 total
includes taxes & fees
9 Nov - 10 Nov
Charming 2-bedroom condo in delightful Chelsea with WiFi, AC
A modern living room with a sofa, a coffee table, and a TV mounted on the wall.

2. Family-Friendly 1BR | Sleeps 6

Family-Friendly 1BR | Sleeps 6
Chelsea
The price is HK$1,091
HK$2,186 total
includes taxes & fees
8 Nov - 9 Nov
Family-Friendly 1BR | Sleeps 6
A modern living room with a flat-screen TV, a grey sofa, and a wooden accent wall.

3. 3 bdrm Apt next to Airport/2

3 bdrm Apt next to Airport/2
Chelsea
The price is HK$1,787
HK$1,962 total
includes taxes & fees
30 Nov - 1 Dec
3 bdrm Apt next to Airport/2
A bedroom with a bed, a nightstand with a lamp, and wall art depicting cityscapes.

4. Mezzanine Apt near Airport Private Parking

Mezzanine Apt near Airport Private Parking
Chelsea
The price is HK$1,591
HK$1,749 total
includes taxes & fees
1 Dec - 2 Dec
Mezzanine Apt near Airport Private Parking
A bedroom with a large bed, two chairs, a potted plant, and a bay window with blinds.

5. 3bdrm Apt next to Airport/Downtown 7 min drive

3bdrm Apt next to Airport/Downtown 7 min drive
Chelsea
8.0 out of 10, Very good, (11 reviews)
"We stayed here overnight for a show at TD Garden. Great price and location for our needs."
United States
Nicole D.
The price is HK$1,787
HK$1,963 total
includes taxes & fees
30 Nov - 1 Dec
3bdrm Apt next to Airport/Downtown 7 min drive
A modern living room with a flat-screen TV on a white stand, a grey sofa, a wooden accent wall, and a hanging light fixture.

6. Modern Apt Near Airport 7 Min to Downtown

Modern Apt Near Airport 7 Min to Downtown
Chelsea
The price is HK$1,450
HK$1,564 total
includes taxes & fees
30 Nov - 1 Dec
Modern Apt Near Airport 7 Min to Downtown
A bedroom with a bed, a bedside table with a lamp, a wall-mounted shelf, and a potted plant.

7. Home for Families | Sleeps 11 | 5 min Downtown

Home for Families | Sleeps 11 | 5 min Downtown
Chelsea
10.0 out of 10, Exceptional, (1 review)
The price is HK$1,983
HK$2,158 total
includes taxes & fees
8 Nov - 9 Nov
Home for Families | Sleeps 11 | 5 min Downtown
A spacious living area with a large sectional sofa, a glass dining table, and multiple windows providing natural light.

8. Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino

Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino
Chelsea
9.4 out of 10, Exceptional, (129 reviews)
"Great stay for a couple of nights. Great location."
United States
Kevin C.
The price is HK$2,949
HK$5,387 total
includes taxes & fees
9 Nov - 10 Nov
Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino
A modern living room with a sofa, dining table, chairs, a coffee table, and a TV displaying streaming services.

9. 1BR for 6 | Parking + Easy Transit

1BR for 6 | Parking + Easy Transit
Chelsea
The price is HK$963
HK$2,024 total
includes taxes & fees
8 Nov - 9 Nov
1BR for 6 | Parking + Easy Transit
A modern living room with a sofa, a dining table with chairs, a coffee table with a plant, and a TV mounted on the wall.

10. 1BR for 6 | Parking + Full Kitchen

1BR for 6 | Parking + Full Kitchen
Chelsea
The price is HK$1,055
HK$2,142 total
includes taxes & fees
8 Nov - 9 Nov
1BR for 6 | Parking + Full Kitchen
A modern living room with a sofa, chairs, a round table, and a large window with a view.

11. Spacious 1BR | Sleeps 6 + Parking

Spacious 1BR | Sleeps 6 + Parking
Chelsea
The price is HK$1,304
HK$2,465 total
includes taxes & fees
17 Nov - 18 Nov
Spacious 1BR | Sleeps 6 + Parking
A modern living room with a sofa, chairs, a coffee table, and a TV mounted on the wall.

12. Comfortable 1BR | Fast WiFi + Parking

Comfortable 1BR | Fast WiFi + Parking
Chelsea
The price is HK$1,091
HK$2,186 total
includes taxes & fees
8 Nov - 9 Nov
Comfortable 1BR | Fast WiFi + Parking
A modern living room with a sofa, chairs, a coffee table, and a painting on the wall.

13. Modern 1BR | Sleeps 6 + Parking

Modern 1BR | Sleeps 6 + Parking
Chelsea
The price is HK$1,082
HK$2,175 total
includes taxes & fees
8 Nov - 9 Nov
Modern 1BR | Sleeps 6 + Parking
A white building with a blue roof, a wooden dock, and a metal staircase leading to a platform.

14. Fun houseboat. Walk to Boston attractions WIFI

Fun houseboat. Walk to Boston attractions WIFI
Boston
9.8 out of 10, Exceptional, (120 reviews)
"The houseboat was great! Everyone was super friendly and helpful. Can’t wait for our next stay!"
United States
Frank M.
The price is HK$968
HK$3,681 total
includes taxes & fees
30 Nov - 1 Dec
Fun houseboat. Walk to Boston attractions WIFI
A kitchen with a bar area, wooden paneling, and a view of a dock.

15. Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep

Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep
Charlestown
9.8 out of 10, Exceptional, (213 reviews)
"Wonderful brief stay!"
United States
Marie T.
The price is HK$941
HK$3,956 total
includes taxes & fees
7 Dec - 8 Dec
Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep
A waterfront building with a sign reading "Turtle," featuring a dock with red chairs and potted plants.

16. Unique Boston Harbor Houseboat Suite 2 - Experience near the Freedom Trail -AC

Unique Boston Harbor Houseboat Suite 2 - Experience near the Freedom Trail -AC
Thompson Square - Bunker Hill
9.8 out of 10, Exceptional, (79 reviews)
"Great communication. The atmosphere was beautiful. Love all the baked goods"
United States
VIaney
The price is HK$2,109
HK$3,614 total
includes taxes & fees
13 Nov - 14 Nov
Unique Boston Harbor Houseboat Suite 2 - Experience near the Freedom Trail -AC
A modern lobby with a wooden panel wall, a beige sofa, a patterned rug, and a large abstract painting.

17. Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (772 reviews)
"Great room: new and spacious. The kitchenette has everything i needed and more."
United States
Yelitza
The price is HK$809
HK$1,855 total
includes taxes & fees
6 Dec - 7 Dec
Global Luxury Suites Downtown Boston
A living room with a grey sofa, a black armchair, a coffee table, and a blue rug. There are two windows with blinds, a bookshelf, and a potted plant.

18. Bright 2BR by Boston Waterfront

Bright 2BR by Boston Waterfront
East Boston
9.6 out of 10, Exceptional, (51 reviews)
"7 min from the airport, seamless check in and entry and a spotless, welcoming place- with coffee! Great rental- perfect if you’re coming/going from Logan"
United States
Bridget
The price is HK$921
HK$2,473 total
includes taxes & fees
11 Nov - 12 Nov
Bright 2BR by Boston Waterfront
A row of brick townhouses with fire escapes, a brick sidewalk, and potted plants.

19. Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.5 star property
Beacon Hill
8.0 out of 10, Very good, (165 reviews)
"Great property in a great location. Tons of food options nearby. Walking distance to Target and Whole Foods. Easy access to the Blue line. The neighborhood was quiet and clean. Boston common is just a block away. Definitely would stay again and highly recommend."
United States
TommyWallace
The price is HK$790
HK$1,629 total
includes taxes & fees
9 Nov - 10 Nov
Maverick Suites at 40 Temple St
A balcony with a city view, featuring a table with wine glasses and a bottle, and a chair.

20. Marriott Vacation Club® at Custom House, Boston

Marriott Vacation Club® at Custom House, Boston
3.5 star property
Downtown Boston
9.4 out of 10, Exceptional, (680 reviews)
"I can’t believe this property is a hotel and not a historic landmark. If you like historical places this is the place to stay in Boston."
United States
Benny
The price is HK$1,792
HK$2,060 total
includes taxes & fees
25 Nov - 26 Nov
Marriott Vacation Club® at Custom House, Boston
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chelsea Hotel Reviews

Seaport Hotel Boston

Seaport Hotel Boston

10/10 Excellent
"Glad we could find a weekend where price wasn’t too bad (for Boston)… it’s a nice property near the water, with good restaurants nearby. Good views, clean, with a rainfall shower. We had a delightful time."
James 1-night trip
Posted 1 hour ago
Seaport Hotel Boston

Find out more about Chelsea

Search for holiday rentals in Chelsea on Expedia! You can easily find your home rentals, villas, holiday apartments in Chelsea using one of the methods below:

  • View our selection of featured holiday rentals in Chelsea
  • Use the map to find apartments and other holiday homes in the Chelsea neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chelsea while they last

Look no further and take a look at our great range of rental properties in Chelsea!

Frequently asked questions

Can I find holiday rentals in Chelsea?

Yes, there are holiday rentals close to the most popular sights in Chelsea, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and shops in Chelsea. While you're here, grab a bite or have a drink at the bars.

What are some of the best holiday rentals that Chelsea has to offer?

Lovely Bright and Spacious 4-bedroom house with 6 off-street parking spots: This holiday home rental outside of Chelsea offers a patio, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with 1 hot tub and a selection of books.

How many holiday rentals will I find in Chelsea?

Choose from 5 Expedia holiday rentals in Chelsea for a memorable holiday.

What’s there to see and do in Chelsea?

While exploring the area, visit family-friendly sights like USS Constitution Museum, or get outside and enjoy nature at Boston Common. In the wider area, you’ll find popular places such as Fenway Park and Encore Boston Harbor.

What’s a holiday rental in Chelsea like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chelsea. Holiday rentals feature extras like WiFi and washers and dryers so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can provide a sense of seclusion away from shared hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for a family trip or a small group gathering.